KENOSHA, Wis. — Maurice James Freeland, 44, the man whose flying kick toward Kyle Rittenhouse was captured on video and seen around the world during the August 2020 Kenosha riots, is married to Jamie Freeland, who works in advertising and revenue generation for the financially troubled Racine County Eye and is now the executive director of Racine’s Senior Companion Program. A comprehensive investigation by Kenosha County Eye into Freeland’s criminal history reveals multiple felony convictions, including two felony escapes, identity theft-related offenses, domestic abuse battery, and operating while intoxicated with a young child in his vehicle.
(Photos by Kenosha County Sheriff’s Office.)
Freeland was publicly identified as the mysterious “Jump Kick Man” during Rittenhouse’s nationally televised 2021 murder trial. A review of 11 Kenosha County criminal cases, court minutes, and criminal complaints reveals that Freeland has faced at least 21 criminal charges in Kenosha County alone, resulting in 12 guilty findings, including six felony convictions.
Racine County Eye, which has absolutely no affiliation whatsoever with Kenosha County Eye, is a left-wing Racine-based blog founded by former Kenosha News “reporter” Denise Lockwood. The publication has faced mounting financial questions after Lockwood issued urgent fundraising appeals and repeatedly asked readers for donations to keep the operation running.
Freeland’s wife, Jamie Freeland, has worked in advertising and revenue generation for Racine County Eye and is now the executive director of the Senior Companion Program, a nonprofit organization serving elderly residents in the Racine area. Private Facebook messages obtained by Kenosha County Eye reveal that Jamie Freeland reached out to the operator of a controversial local Kenosha hate blog, seeking help generating advertising revenue for Racine County Eye and discussing plans to expand the publication into Kenosha.
During that conversation, Jamie Freeland confirmed her husband’s connection to one of the most widely publicized moments of the Kenosha riots. “My husband is jump kick man from the Kyle Rittenhouse events,” she wrote on July 1, 2025.
The Man Seen Around The World
On August 25, 2020, during the violent riots that followed the police shooting of Jacob Blake, Kyle Rittenhouse was running down Sheridan Road when he fell to the pavement and was confronted by several individuals. One man ran toward Rittenhouse, jumped into the air, and delivered a flying kick toward his head as Rittenhouse attempted to defend himself.
The encounter was captured on video and became one of the most recognizable moments of the Rittenhouse shootings. Rittenhouse fired two shots toward the man, missing both times, and the individual escaped the scene without being struck.
The individual became known throughout the subsequent criminal proceedings as “Jump Kick Man” because his identity was not publicly established during the trial. In November 2021, Fox News reported that Rittenhouse’s defense attorneys identified the man as Maurice Freeland, who was 39 at the time.
Fox News also reported that Freeland had approached prosecutors about testifying in exchange for immunity on other criminal matters, including an outstanding OWI prosecution. Prosecutors reportedly declined the proposed arrangement, and Freeland never testified during the trial.
Rittenhouse was ultimately acquitted of all charges stemming from the shootings. Freeland’s participation in the confrontation, however, remained part of the nationally circulated video evidence that helped define the events of that night.
A Family Connection To Racine County Eye
The connection between Freeland and Racine County Eye came to light through a series of Facebook messages exchanged on July 1, 2025, between Jamie Freeland and the operator of a controversial Kenosha-based hate blog. Jamie initiated the conversation by identifying herself as a representative of Racine County Eye and explaining that the publication was attempting to expand into Kenosha through a project called The Kenosha Lens.
Jamie Freeland specifically requested assistance locating businesses willing to purchase advertising, explaining that she was responsible for advertising sales at Racine County Eye. She described her previous employment at Southern Lakes Newspapers, the Journal Times, and the Kenosha News before joining Racine County Eye.
“Thank you we are trying if you know of any businesses looking to advertise let me know I’m the sole person at Racine county eye that sells advertising so I could use any leads :)” she wrote.
Jamie Freeland also explained that her goal was to increase the publication’s revenue sufficiently to hire additional journalists and expand into Kenosha. The messages establish that she was actively seeking assistance from the operator of a local hate blog to generate advertising business for Racine County Eye.
During the exchange, Jamie confirmed that Maurice Freeland was her husband and identified him as the man nationally known as “Jump Kick Man.” The conversation occurred approximately nine months before Racine County Eye’s widely publicized financial emergency and fundraising appeals in the spring of 2026.
(Photo: Facebook.)
On July 30, 2026, Racine County Eye reported that Jamie Freeland had been appointed executive director of Racine’s Senior Companion Program. The appointment placed her in a leadership position at a nonprofit organization that provides companionship and assistance to older residents in the Racine community.
Racine County Eye’s Financial Difficulties
The connection comes as Racine County Eye has faced substantial questions about its financial stability. In late March 2026, Lockwood emailed supporters describing an emergency funding situation and warning that the publication needed to raise $5,000 within 72 hours and $20,000 by April 30 to continue operations.
(Photograph: LinkedIn)
The appeal offered limited explanation about what had caused the financial emergency or how the requested donations would resolve the publication’s financial difficulties. Kenosha County Eye subsequently asked Lockwood whether the fundraising goals had been achieved, whether the publication’s finances had stabilized, and whether the operation remained financially sustainable, but those inquiries went unanswered.
Meanwhile, Racine County Eye launched a separate $15,000 fundraising campaign for its 2026 election coverage. As of April 30, the campaign had collected just $87 from two donors, and by June 24, that figure had increased to $1,658 from 20 donors, still substantially below the stated fundraising goal.
The publication continued sending fundraising emails promoting its election coverage as nonpartisan, despite questions about Lockwood’s political affiliations and the publication’s editorial perspective. Whether Racine County Eye ultimately met its emergency fundraising targets remains unclear, and the publication has not publicly provided a complete accounting of its financial condition.
The fundraising history provides additional context to Jamie Freeland’s earlier efforts to locate advertisers and expand the operation into Kenosha. Her messages specifically connected the need for additional revenue to Racine County Eye’s ambition to hire reporters and establish a larger presence in Kenosha County.
Freeland’s Criminal Charges: A Look At The Record
Kenosha County Eye obtained and reviewed criminal complaints and court records covering 11 separate Kenosha County criminal cases filed against Maurice Freeland between 2000 and 2021. Those cases collectively involved 21 criminal counts, with some resulting in convictions and others being dismissed, amended, or dismissed and read in as part of plea agreements.
The following is a list of criminal charges filed against Freeland, not a list of convictions:
- 2000: One felony escape charge.
- 2007: One felony possession of THC, second or subsequent offense, charged with an enhancement for possession near a park.
- February 2008: One misdemeanor theft charge involving a purse stolen from the Kenosha Public Library.
- March 2008: Five felony counts of unauthorized use of another person’s identifying information involving a stolen debit card.
- August 2008: One felony escape charge after Freeland left a court-authorized work crew without permission.
- 2009: One felony count of operating a motor vehicle without the owner’s consent and one misdemeanor count of obstructing an officer, both originally charged with repeater enhancements.
- 2013: One felony count of possession with intent to deliver marijuana near a park, with a repeater enhancement, and one misdemeanor count of obstructing an officer.
- 2016: One misdemeanor count of disorderly conduct with domestic abuse and repeater modifiers.
- 2017: One misdemeanor count of disorderly conduct with a repeater enhancement.
- 2020: Three misdemeanor counts involving battery, criminal damage to property, and disorderly conduct, all with domestic abuse modifiers.
- 2021: Three misdemeanor counts involving operating while intoxicated with a child younger than 16 in the vehicle, disorderly conduct with a domestic abuse modifier, and possession of THC.
The sheer number of cases documents a criminal history spanning more than 25 years, beginning when Freeland was still a teenager. Court records also show repeated probation revocations, prison and jail sentences, and numerous plea agreements in which prosecutors dismissed or amended charges.
2000 — Felony Escape — Two Years In Prison
Kenosha County Case No. 2000CF000956 was filed September 26, 2000, when Freeland was just 18 years old. He was charged with felony escape in connection with an incident on September 15, 2000, marking his earliest identified Kenosha County criminal prosecution.
On January 11, 2001, Freeland entered a guilty plea before Kenosha County Circuit Court Judge David Bastianelli. On February 13, 2001, Bastianelli sentenced Freeland to two years in state prison followed by five years of extended supervision.
The original criminal complaint was not available for review, so the specific circumstances surrounding the escape could not be independently reconstructed. The CCAP record, however, confirms both the felony conviction and the prison sentence imposed by Bastianelli.
2007 — Felony Drug Charge Reduced To Misdemeanor
Kenosha County Case No. 2007CF000591 involved a May 30, 2007, encounter with officers assigned to the Kenosha Police Department’s Street Crimes Unit. Officers had received information about a man selling marijuana near the Uptown Pantry, and Freeland reportedly matched the description provided to investigators.
Police stopped Freeland near 61st Street and 22nd Avenue while he was riding a bicycle, and an officer asked if he was carrying anything illegal. According to the criminal complaint, Freeland admitted he had marijuana in his coat pocket, and officers recovered approximately 1.9 grams of marijuana that Freeland claimed was for personal use.
Prosecutors originally charged Freeland with felony possession of THC as a repeat offender, with an enhancement based on the offense occurring near Wilson Triangle Park. The charge was subsequently amended to misdemeanor marijuana possession as part of the case’s resolution.
On July 24, 2007, Judge Dennis Barry accepted Freeland’s guilty plea and imposed a four-month jail sentence, which was stayed. Freeland was placed on one year of probation and received a six-month driver’s license revocation.
2008 — Stolen Purse At Kenosha Public Library
Kenosha County Case No. 2008CM000349 stemmed from the theft of a purse at Simmons Library in downtown Kenosha on February 23, 2008. According to the complaint, the woman had been working on her taxes at a library computer when her purse disappeared from beside her workstation.
The purse contained personal identification, bank cards, a cellular phone, eyeglasses, car keys, and tax documents. Investigators reviewed library surveillance footage showing a man taking a bundle from the woman’s workstation, concealing it beneath a jacket, and leaving the library.
Police subsequently located Freeland, who admitted taking the purse but denied removing anything from it. He told investigators he discarded the purse in a dumpster near Fonte Foods, while detectives continued investigating fraudulent transactions involving the woman’s debit card.
Freeland was charged with misdemeanor theft, but the case did not result in a separate criminal conviction. On April 14, 2008, Judge Wilbur Warren III dismissed the theft charge but read it in during the resolution of a related felony prosecution involving the victim’s identifying information.
2008 — Five Felony Identity Theft-Related Charges
Kenosha County Case No. 2008CF000331 developed from the same stolen purse investigation and involved considerably more serious criminal charges. Prosecutors accused Freeland of using the woman’s stolen debit card during five separate transactions at Kenosha businesses, including gas stations, convenience stores, and a beauty supply store.
The transactions occurred on the same afternoon the purse was stolen from Simmons Library. Prosecutors subsequently charged Freeland with five Class H felonies involving unauthorized use of another person’s personal identifying information to obtain goods or money.
On April 14, 2008, Freeland pleaded guilty to two felony counts before Judge Wilbur Warren III. The remaining three felony counts were dismissed but read in, leaving Freeland with two felony convictions from the prosecution.
Warren initially withheld sentence and placed Freeland on three years of probation, with six months in the Kenosha County Jail imposed as a condition. The arrangement did not last, however, as Freeland’s probation was subsequently revoked and the case returned to court for sentencing.
On March 1, 2010, Warren sentenced Freeland to two years of initial confinement in state prison followed by two years of extended supervision. The sentences on the two felony counts were ordered to run concurrently, and the case also involved restitution for the financial losses associated with the offenses.
2008 — Escaped From Work Crew While Serving Sentence
Kenosha County Case No. 2008CF000938 involved another felony escape, this time while Freeland was already serving a jail sentence connected to his earlier convictions. Freeland had been allowed to participate in a work crew at the Kenosha Achievement Center, where he was supposed to report for work at 7 a.m. and return to the Kenosha County Detention Center at 4:30 p.m.
According to the criminal complaint, Freeland left his assigned work area for a break on July 26, 2008, and never returned. Supervisors subsequently discovered that he was missing, and as of late July 27, he still had not returned to the detention center.
Prosecutors charged Freeland with felony escape, and on September 17, 2008, he pleaded guilty before Judge Barbara Kluka. It was the second felony escape conviction documented in his Kenosha County criminal history.
On October 23, 2008, Kluka sentenced Freeland to one year in the Kenosha County Jail. The first four months were to be served without work release, while work release was authorized for the remaining portion of the sentence.
2009 — Stolen Minivan Near Kenosha Hospital
Kenosha County Case No. 2009CF001333 involved the December 5, 2009, theft of a Chrysler Town & Country minivan near Kenosha Hospital. According to the criminal complaint, a man parked the vehicle near the hospital while picking up his wife and returned approximately ten minutes later to discover that it had disappeared.
The minivan’s owner reported that approximately $700 in cash was inside the vehicle, including money intended for rent. Investigators reviewed hospital surveillance footage that captured a man near the minivan immediately before it disappeared and subsequently identified Freeland as a suspect.
According to the complaint, Freeland initially denied stealing the vehicle but later admitted taking it, driving around Kenosha, abandoning it near a flea market, and discarding the keys. He also acknowledged that his original statement to investigators was untruthful.
Prosecutors charged Freeland with felony operating a motor vehicle without the owner’s consent and misdemeanor obstructing an officer, both with repeater enhancements. On January 14, 2010, Freeland pleaded guilty to the felony before Judge Barbara Kluka, while the obstructing charge and felony repeater enhancement were dismissed.
On June 17, 2010, Kluka imposed and stayed a five-year prison sentence consisting of three years of initial confinement and two years of extended supervision. Rather than immediately requiring Freeland to serve the prison sentence, Kluka placed him on three years of probation, consecutive to his earlier identity-information case, and ordered restitution of $1,000.
2013 — Marijuana, Police Chase And Another Felony Conviction
Kenosha County Case No. 2013CF000244 stemmed from a March 3, 2013, investigation conducted by members of the Kenosha Police Department’s Gang Crimes Unit. Officers were conducting surveillance near a residence suspected of involvement in drug activity when they observed Freeland enter the building and leave shortly afterward.
When officers approached Freeland, he fled on foot, leading police through residential yards before being apprehended after slipping on ice. According to the complaint, officers subsequently used a police K-9 to search the area where he had run and recovered a bag containing ten individually packaged quantities of marijuana weighing approximately 18.05 grams.
Prosecutors originally charged Freeland with felony possession with intent to deliver THC near Columbus Park, with a repeater enhancement, along with misdemeanor obstructing an officer. The felony drug charge was subsequently amended to possession of THC, second or subsequent offense, with the repeater modifier.
On May 10, 2013, Freeland pleaded guilty to both counts before Judge Anthony Milisauskas. Milisauskas sentenced him to six months in the Kenosha County Jail on each count, to be served concurrently, without work release.
2016 — Domestic Abuse Case Involving Former Wife
Kenosha County Case No. 2016CM000282 involved a March 7, 2016, domestic disturbance between Freeland and his then-estranged wife. According to the criminal complaint, the woman reported that Freeland drove a minivan toward her vehicle at a high rate of speed while she was attempting to exit it, forcing her to jump back inside to avoid being struck.
The woman told investigators that Freeland drove past the residence a second time and began shouting comments about her personal life and relationship. Freeland denied wrongdoing when arrested, but prosecutors charged him with misdemeanor disorderly conduct with domestic abuse and repeater modifiers.
On April 8, 2016, Freeland pleaded guilty before Judge Bruce Schroeder, who withheld sentence and placed him on two years of probation. The probation was subsequently revoked, requiring Freeland to return to court for sentencing.
On March 15, 2018, Freeland was sentenced to 120 days in the Kenosha County Jail following the probation revocation. The court also imposed eight days for unpaid financial obligations, concurrent with the jail sentence.
2017 — Road Rage Incident And Another Probation Revocation
Kenosha County Case No. 2017CM000539 stemmed from a March 23, 2017, road rage confrontation involving several individuals and a woman driving near 52nd Street in Kenosha. According to the complaint, the woman reported being followed by occupants of a Ford Explorer after a traffic dispute and said several people confronted her near a gas station.
The woman told police that individuals exited the Explorer, shouted at her, and engaged in threatening behavior. The complaint attributed a thrown bottle and physical contact with the woman to other occupants, while Freeland was identified as the man who exited the Explorer and pounded on the window of her vehicle after she followed it to photograph the license plate.
Prosecutors charged Freeland with misdemeanor disorderly conduct as a repeat offender, and on July 28, 2017, he pleaded guilty before Judge David Bastianelli. The repeater enhancement was removed, and Freeland received six months of probation rather than an immediate jail sentence.
That probation was subsequently revoked, bringing Freeland back before the court. On March 1, 2018, Bastianelli sentenced him to 60 days in the Kenosha County Jail.
2020 — Domestic Abuse Battery Conviction
Kenosha County Case No. 2020CM000415 involved a March 23, 2020, domestic disturbance after a woman called Kenosha Police and reported that her boyfriend, Maurice Freeland, had beaten her. According to the criminal complaint, the couple had been drinking earlier in the evening when the woman took Freeland’s car keys because she believed neither was in a condition to drive safely.
The woman told investigators that Freeland became angry after they returned home, punched holes in the drywall, and struck her several times in the chest. She also reported that he threw her to the kitchen floor, kicked her in the rib cage, damaged a television, and broke her cellular phone.
According to the complaint, the woman fled from the residence after Freeland threatened to kill her. Responding officers observed dried blood around her shirt collar and damage to the drywall, corroborating portions of her account.
Prosecutors charged Freeland with three misdemeanor offenses: battery, criminal damage to property, and disorderly conduct, all with domestic abuse modifiers. On June 29, 2020, Freeland pleaded guilty to domestic abuse battery before Judge Mary Kay Wagner, while the remaining two charges were dismissed but read in.
Wagner withheld sentence and placed Freeland on 12 months of probation, but that probation was later revoked. On August 16, 2021, Freeland was sentenced to seven months in the Kenosha County Jail, with work release permitted.
2021 — OWI With Young Child In Vehicle, Domestic Abuse Allegations
Kenosha County Case No. 2021CM000608 involved a May 30, 2021, crash in which Freeland drove a black sedan into a utility pole along Sheridan Road in the Village of Somers. Inside the vehicle were Freeland, an adult female passenger, and his six-year-old son.
According to the criminal complaint, Freeland admitted that he had been driving and told deputies he had smoked marijuana several hours earlier. Investigators described Freeland as having extremely bloodshot eyes and exhibiting signs of impairment during field sobriety testing.
Witnesses also reported that Freeland became aggressive toward the female passenger following the crash. One witness told deputies that Freeland grabbed the woman by her hair, led her around the vehicle, and yelled at her about what to tell police, although the woman initially denied being assaulted before later acknowledging that he had pulled her hair.
Prosecutors charged Freeland with operating while intoxicated with a passenger younger than 16, disorderly conduct with a domestic abuse modifier, and possession of THC. The prosecution remained unresolved for nearly five years before Freeland entered a guilty plea in February 2026.
On February 17, 2026, Freeland appeared before Kenosha County Circuit Court Judge Jodi Meier and pleaded guilty to operating while intoxicated with a child younger than 16 in the vehicle. At the prosecution’s request, the domestic abuse disorderly conduct and marijuana possession charges were dismissed.
Meier sentenced Freeland to 30 days in the Kenosha County Jail, with four days of credit and work release permitted. She also imposed a $500 fine, a 12-month driver’s license revocation, a 12-month ignition interlock requirement, and an alcohol assessment, with Freeland ordered to report to jail on March 14, 2026.
A Criminal History Spanning More Than 25 Years
The court records document a man whose repeated encounters with the criminal justice system began when he was a teenager and continued well into adulthood. His convictions include felony escape, felony misuse of identifying information, felony operating a vehicle without the owner’s consent, felony drug possession, misdemeanor obstruction, disorderly conduct, domestic abuse battery, and operating while intoxicated with a young child in his vehicle.
Several cases initially resulted in probation, only for Freeland to return to court after that probation was revoked. Other cases resulted in prison or jail sentences, while several serious original charges were dismissed or reduced as part of plea negotiations.
The criminal history also provides additional context to Freeland’s identification as the mysterious man who attacked Kyle Rittenhouse during the 2020 Kenosha riots. At the time of the nationally televised trial in November 2021, Freeland already had multiple felony convictions and was facing unresolved criminal charges involving operating while intoxicated with a child passenger, domestic abuse disorderly conduct, and marijuana possession.
His wife, meanwhile, later sought advertising leads from the operator of a local Kenosha hate blog to help generate revenue for Racine County Eye, a financially troubled publication seeking to expand its presence into Kenosha. Her messages confirm both her role in the publication’s revenue-generating efforts and her statement that she was married to the man nationally identified as “Jump Kick Man.”
For years, millions of Americans knew Maurice Freeland simply as the unidentified man who delivered a flying kick toward Kyle Rittenhouse during one of the most consequential nights in Kenosha’s recent history. His extensive criminal record, repeated felony convictions, history of probation revocations, and family connection to Racine County Eye now provide a far more comprehensive picture of the man behind the nationally recognized nickname.
